Greene, 55, rose from middle-class origins to make millions investing in real estate. Then he made hundreds of millions by betting that the real estate bubble would burst and investing in credit-default swaps. He’s running as an outsider, and his bio is unconventional for a politician, with cameos by Mike Tyson as best man at Greene’s 2007 wedding and Heidi Fleiss as a yearlong houseguest. (“We weren’t dating,” Greene told Forbes in a 2008 profile.)